4-(Chlorosulfonyl)benzoic acid → 4-[3-(Methanesulfonyl)pyrrolidine-1-sulfonyl]benzoic acid

HRID 1676953Notes

Reaction equation

HRID 1676953 reaction equation
Cl[S:2]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[CH3:14][S:15]([CH:18]1[CH2:22][CH2:21][NH:20][CH2:19]1)(=[O:17])=[O:16]>>[CH3:14][S:15]([CH:18]1[CH2:22][CH2:21][N:20]([S:2]([C:5]2[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=2)(=[O:4])=[O:3])[CH2:19]1)(=[O:17])=[O:16]

Participants

3

Reactant 2

HCID 823854-(Chlorosulfonyl)benzoic acidHCID 34193563-(methylsulfonyl)pyrrolidine

Product 1

HCID 671764464-[3-(Methanesulfonyl)pyrrolidine-1-sulfonyl]benzoic acidYield 44.1%

Procedure

The title intermediate is prepared from 4-(chlorosulfonyl)benzoic acid (CAS 10130-89-9) (375 mg, 1.7 mmol) and 3-(methylsulfonyl)pyrrolidine (CAS 433980-62-2) (343 mg, 2.3 mmol) in a manner substantially similar to Procedure F to provide 250 mg (44%) of the title compound. MS (ES−) 332.0 (M−H)−.

Sources & evidence

ORD record
ord-81b09e6f99174fd0a0c61c2c1e70c410
Source dataset
uspto-grants-2011_08
Patent number
US08008296B2

Reaction notes

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